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Lisa M. Doyle, Shane O’Sullivan, Claudia Di Salvo, Michelle McKinney, Patrick McArdle and Paul V. Murphy
2017
October
Organic Letters
Stereoselective epimerizations of glycosyl thiols
Published
()
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19
5802
5805
Glycosyl thiols are widely used in stereoselective S-glycoside synthesis. Their epimerization from 1,2-trans to 1,2-cis thiols (e.g., equatorial to axial epimerization in thioglucopyranose) was attained using TiCl4, while SnCl4 promoted their axial-to-equatorial epimerization. The method included application for stereoselective β-d-manno- and β-l-rhamnopyranosyl thiol formation. Complex formation explains the equatorial preference when using SnCl4, whereas TiCl4 can shift the equilibrium toward the 1,2-cis thiol via 1,3-oxathiolane formation.
http://dx.doi.org/10.1021/acs.orglett.7b02760
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